


All Dressed Up

by within_a_dream



Series: Kinktober 2018 [6]
Category: Miss Fisher's Murder Mysteries
Genre: Crossdressing, Multi
Language: English
Status: Completed
Published: 2018-10-11
Updated: 2018-10-11
Packaged: 2019-07-29 14:06:19
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,603
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16265762
Author URL: https://archiveofourown.org/users/within_a_dream/pseuds/within_a_dream
Summary: Hugh has to dress up for an undercover investigation, and this leads to new developments in his relationship





	All Dressed Up

Hugh would have preferred Miss Fisher to answer the door a little less cavalierly, considering that he was sitting in her parlor wearing rouge, lipstick, and a scandalously short-hemmed dress. He didn't know why he'd agreed on the dress in the first place—well, he did. There had been a crime in a certain type of club, and Inspector Robinson had looked at Hugh calm as anything and said, "We'll need to blend in, and I don't look half as good in a dress."

It was true that Hugh had trouble picturing Jack wearing anything remotely feminine, although he still resented the implication that he ought to be the dame of the group. He’d never been more uncomfortable than he was now, wearing high heels, a sparkling red dress with matching lipstick, and underneath it all the silk panties that Miss Fisher had insisted were necessary, even after Hugh protested that no one would be seeing under his skirt if he could help it.

And now here he was, far too exposed with only an open door between him and the rest of the world.

“I know I’m home early…” an all-too-familiar voice said, and Hugh tried to duck out of the parlor. “Is that--” Dot caught sight of him, and her jaw dropped.

“Beautiful, isn’t he?” Miss Fisher sounded entirely too happy about the situation.

“There was an investigation--I wasn’t--I don’t--” Hugh couldn’t manage to stutter out a full explanation, and he was sure his face would be blazing red even without the rouge. “I should change.”

“Leave it on.” Dot looked startled by her own boldness. “It _does_ look rather nice on you.”

The thought of Dot admiring the way the sleek satin dress clung to him affected Hugh more than he’d care to admit--and then his cock began to strain at the skirt, and he could tell that Dot noticed.

“You ought to help him out,” Miss Fisher murmured, and if Hugh had been flustered before, now he wasn’t even sure if he could speak.

Dot’s mouth formed a perfect, silent _O_. “I’m not sure I know how, Miss.”

“Allow me to demonstrate.” She strode up to Hugh and flung the wig off, running her fingers through his hair. She kissed his cheek and then his neck, pausing to suck at the skin just above his collarbone until he let out a moan.

Then she kissed him square on his red-smeared lips, and slipped a knee between his legs. Hugh rutted against her, too desperate to care about the embarrassment he knew would follow, and after an embarrassingly short time, he gasped and fell against Miss Fisher as he spent himself.

“What’s going on down here?” Inspector Robinson asked, coming down the stairs from the bathroom. He took in Hugh, lipstick smeared and a rather conspicuous stain forming on the front of his dress, and shook his head. “Did you intend to leave me out of it?”

“I certainly wouldn’t mind you joining in, sir.” Oh, he should _not_ have said that. He cast a desperate glance to Dot, who looked surprisingly eager at the prospect.

Jack raised an eyebrow. “You’re certain of that? Both of you?”

“Yes,” Dot said a bit too quickly, adding “So long as Hugh is, of course” as an afterthought.

Hugh shut his eyes, trying to clear his head. It wouldn’t be impossible to turn back now, pretend this never happened. He was drunk, he was tired, and this was ridiculous enough to be passed off as a dream--an orgy, with his boss and his fiancée’s employer? But...he didn’t want to say no. Far from satisfying him, Miss Fisher’s attentions had only made his appetite grow, and the naked lust in Jack’s eyes certainly wasn’t helping matters.

“I’m sure,” he said.

“Unless you’d like Mr. Butler to stumble across us when he makes the morning tea, I suggest we retreat to the bedroom.” Phryne put a hand on Hugh’s shoulder, guiding him to the stairs. As much as he hated to admit it, Hugh was still a bit wobbly from his earlier orgasm (and if it ever came up in conversation, he’d be sure to emphasize the seduction and minimize the bit where he’d come in his underwear).

As soon as they were through the door, Jack pinned him against the wall, kissing him fiercely.

“I’ve wanted to do this since I first saw you tonight.” This was as much a confession as a flirtation, Hugh recognized. They’d all given themselves over to this, with the tacit understanding that they were leaving their reputations in each other’s hands.

Jack hitched the dress up, and Hugh scrambled for the buttons on Jack’s trousers. Together they managed to mostly undress Jack, although when Hugh moved to shrug off his dress, Jack stopped him, rasping, “Leave it on.”

“We’ll ruin it!”

Miss Fisher, lounging on the bed, laughed. “I’ve put dresses through worse, and they’ve still come clean at the laundry.”

Jack cocked an eyebrow, a clear _There you have it_. Then he took his eyes off of Hugh for a moment to turn towards the bed. “Phryne, you wouldn’t happen to have any of the…”

She tossed him a container, which he caught handily. Then he brushed a lock of sweat-soaked hair from Hugh’s forehead, leaning in to kiss him.

“I’m going to fuck you,” he said, voice calm and matter-of-fact. “First with my fingers, then with my cock, until those pretty red lips are screaming my name.”

“ _Please_ ,” Hugh said—all he could manage at the moment. Jack smeared his fingers in the salve inside the tin (Vaseline, from the looks of it), and slipped past the silk panties to begin sliding gently into his ass.

Jack was slow, and patient, and Hugh had to wonder how much experience he had with this. Although he wasn’t able to wonder for long—it was hard enough to focus on staying upright with Jack’s hands doing nearly unbearable things to him. Each crook of Jack’s finger drew another whimper from Hugh, and he could see that on the bed, Miss Fisher was slipping her own hand under Dot’s collar.

Hugh tried to split his attention between the cool smile on Jack’s face and Dot’s increasingly reddening complexion, but he soon found himself focusing entirely on Jack’s hand on his waist and the stuttering slide of his fingers. Then he withdrew his hand entirely, and Hugh whined.

“Oh, hush,” Jack said. “I’m going to give you something better.” True to his word, he pressed his cock into Hugh in one smooth motion, making him gasp with the size of it.

Jack paused, brushing a bit of Hugh’s hair out of his face. “Is this all right?”

“If you don’t start moving immediately, I’m going to scream.”

Mercifully, he followed Hugh’s orders. The slick slide of Jack inside him was better even than Hugh had imagined it would be. He moved agonizingly slowly, brushing a thumb over Hugh's nipple and making him moan.

"Faster, please," Hugh murmured, blushing.

Jack bent down to kiss him, nipping at his lip. "I didn't hear that. You'll have to speak up."

"Faster!" Hugh bucked up into Jack's thrusts, which mercifully began to hasten.

"A pretty picture, aren't they?" Miss Fisher’s hand had crept to join Dot’s between her legs. "Here, dear, let me help with that."

Hugh wasn't sure where to look, at Dot's open-mouthed pleasure or Jack biting his lip and nearly overcome. Between the two of them, it wasn't long before he spent himself all over Miss Fisher's beautiful dress once again. Jack soon followed suit, spilling into Hugh and then pulling away with another kiss.

“You should tend to your fiancée,” he said, tracing the outline of Hugh's lips with his finger.

Hugh, still trying to catch his breath, said, “I’m not sure I can.”

At the same time, Dot said, “Oh, we couldn’t! Imagine what would happen if we had to move the wedding earlier.”

Miss Fisher laughed. “After all we’ve done, you still have such a narrow imagination. Hugh, come here. There’s more than one way to please a woman.”

Hugh sprawled himself across the bed between Dot's legs, following Miss Fisher's directions. He pressed his lips to the folds of her pussy, hesitantly licking at her.

"More," Dot gasped, and oh, Hugh might be getting hard for the third time tonight. She grabbed at his hair and pulled him in closer, and he worked his tongue deeper into her. God, she was wet, and eager, begging for him. It went straight to his cock, knowing that she got this worked up watching him.

Miss Fisher bent down to press a kiss to Dot's breast, and Hugh revised that thought—from watching him, among other things.

"Up a bit, Hugh," Miss Fisher said, nudging at his neck. He followed her order, wrapping his lips around Dot's clit and sucking.

Dot moaned, pushing his head into her with a shudder. One more suck, and she was falling to pieces under him, shouting his name.

Hugh almost wished it had lasted longer. But he was tired, and they'd have plenty of time for more of this later.

As if reading his mind, Miss Fisher pulled him in for a kiss. "We'll have to do this again sometime."

"Oh, yes," Dot gasped, giggling.

The bed was big enough for all of them. Hugh woke up the next morning tangled up in three people's limbs, lipstick smeared on his face and the pillow under him and incredibly grateful he'd let himself be talked into putting on the dress.

 

**Author's Note:**

> A fic for [Kinktober](http://withinadream27.tumblr.com/post/171110050839/kinktober-2018), for the prompt "crossdressing".


End file.
